Associate Director, Contracts

Odyssey Systems has an exciting opportunity for an Associate Director of Contracts to join our growing team. Reporting directly to the Executive Director of Contracts and Compliance, this role leads, develops, and manages a team of Contract Administrators who support a broad spectrum of contracting and procurement functions. The ideal candidate will bring deep expertise in federal contracting, primarily within professional services, and a strong leadership, team development, and regulatory compliance background. This full-time position is based at our corporate office in Wakefield, MA, with a requirement of three days per week in the office.

Duties include, but not limited to:

Oversee the full lifecycle of contracts, subcontracts, licenses, leases, NDAs, and Teaming Agreements - including negotiation, administration, modification, and closeout
• Ensure compliance with applicable regulations and company policies; provide regular reporting on contract status and risk
• Lead development of proposal content for competitive bids and shape contract and negotiation strategies
• Perform risk assessments and support the resolution of contract-related issues
• Drive continuous improvement through the development and implementation of streamlined processes and best practices
• Represent the Contracts function in executive-level meetings; provide strategic insights on pricing, risk, and compliance
• Provide effective leadership and guidance to the Contracts team, ensuring high performance and professional growth
• Stay current with changes in federal acquisition regulations and contracting best practices
• Create tools and processes to improve the efficiency and accuracy of contracting activities
• Recruit, train, and retain top contracting talent; complete annual performance reviews and set strategic goals for staff
• Collaborate with Capture and Proposal teams from RFP release through contract award to ensure responsive, compliant, and competitive submissions
• Negotiate and administer various types of federal contracts (FFP, CPFF, CPAF, T&M, LOE, etc.) across a wide range of programs
• Monitor contract performance to ensure compliance with terms, deliverables, and funding thresholds
• Support audits and ensure all contractual documentation meets internal and external standards

Citizenship: Must be a US citizen

Minimum Required Qualifications

Clearance: Top Secret

Education: Bachelor's degree in Business Administration, Contract Management, Law, or a related field.

Years of Experience: At least ten years of federal contracting experience. At least five (5) years of experience leading contract teams or acquisition staff

Certifications: CFCM certification is preferred

Technical Skills

• Deep knowledge of FAR, DFARS, export compliance, source selection, and price analysis
• Experience with Deltek Costpoint is preferred

Interpersonal Skills

• Leadership: Proven ability to lead, mentor, and manage high-performing teams

• Collaboration: Works effectively across departments and with executive leadership

• Communication: Clear, professional communicator-both written and verbal

• Problem Solving: Resolves challenges with sound judgment and strategic thinking

Additional Information

Location: Wakefield, MA (Corporate office)

Travel: 15%

Remote, Onsite, or Hybrid: Hybrid - three days a week in office

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Odyssey Systems Consulting Group, is an innovative small business committed to providing world-class technical, management, and training support services to government and public sector clients. We focus on people, processes, and performance to deliver superior results. Since our inception in 1997, our commitment to mission success and customer satisfaction has been recognized with exponential growth and exceptional past performance ratings. We accept challenging assignments and drive projects from the planning stages, through implementation, and into operations and support.

Please note: Final compensation for this position will be determined by various factors such as the Federal Government contract labor categories and contract wage rates, relevant work experience, specific skills and competencies, geographic location, education, and certifications.

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities